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The Masked Man is a recurring character whose main characteristic is the use of The Mask. His intentions are unknown, not being clear if he wants to help Jay and hurt Alex Kralie or if he is just trying to use one or both of them. Some believe he is totheark because he is seen in a few of his videos. He's called "Masky" by the fandom.

Far into the series, we learn that there are multiple masked people. The second most prominent masked person is the Hooded Man, and they seem to be working together.

Personality

The Masked Man appears to be angry and has limited vision. He is quick to attack what appears to be threatening him.

Appearances

Warning If you don't want the contents of an entry to be spoiled, do not look at the corresponding entry appearance description.

The Masked Man first appears in Entry 18, when Jay goes to The House. He attacks Jay, and after a quick struggle falls to the ground while having a seizure. Jay carefully approaches him to remove his mask, but he shouts "No!", pushes him away and flees.

During Entry 33, he slips into Jay and Jessica's hotel, enters Jay's room and seemingly attacks him. Jay hits him with a flashlight and flees with the recently found tapes. He's briefly seen limping, as it is confirmed in Entry 35. Some people says teleportation happens when Jay escapes. More info in Entry 33's Observations section.

In Entry 35, the Masked Man attacks Jay and Alex and, upon Jay's removal of the mask, it is confirmed that The Masked Man is in fact Tim. After Alex is stabbed by Tim in the leg and is denied the knife by Jay, he smashes and subsequently breaks Tim's leg. This explains the Masked Man's limp in Entry 33.

After some time out of the series, his face appears again in totheark's "Sidenote", along with who appears to be the Hooded Man. Appears again in totheark's "Extraction".

In Entry 50, the Masked Man is chased by Jay after being spotted lurking behind a tree. Jay is not able to catch him, despite his limping, which made some people reaffirm he has the ability to teleport. Jay loses him when he goes into The Tunnel.

During the events of Entry 52, he saves Jay and Jessica's lives by tackling Alex, who is pointing a gun at them and looks like he is about to murder them. While they struggle, Jay and Jessica escape. A gunshot is heard and Jessica screams, but we don't learn what happened with Alex nor the Masked Man. If you look closely, you can spot the Masked Man already waiting in the place Alex is luring Jay and Jessica. He can be seen peeking out of the window at 3:21.

** After this point The Masked Man is often refered to as a "state of being" because of Entry 53 it is debated whether it is a dissociative personality disorder or something else, but aside from being the same person, we refer to Tim as being different from The Masked Man. For appearances purposes we will now refer to it as a Masked Man state if "both" are in an entry.**

In Entry 62 Jay goes after Tim, but encounters him in his Masked Man state, when he wakes up after the encounter Tim had reverted back to his "usual" persona.

During Entry 67 Tim attacks Alex without his Mask on, however, because he "wakes up" (like the previous entry) later next to his mask, he is believed to be in his Masked Man state.

In Entry 76 from footage found in Entry 75 it shows The Masked Man carrying Jessica out of the hotel they stayed at in The Missing Seven Months and takes her to Rosswood Park. Later in the entry, Tim or possibly him still in the Masked Man state removes the mask.

Speculation

As shown in Entry 35 the Masked Man is without a doubt, or one of them and he is executed in front of J… but the guys doing it looked like pros, could there be more of these situations? (Note: this theory has been proven false in Entry 36. Jay explicitly states the Alex broke Masked Man's leg then left him.)

In many entries it can be seen that video and audio distortion as well as amnesia occurs around the Masked man in a similar fashion to encounters to The Operator.
Possible reasons for this are:
The Masked Man has powers similar to The Operator
(how this occurs can have any number of theories)
The Operator is always present but hidden wherever Masky is
People who have had prolonged exposure to the effects of the The Operator's influence may begin to exhibit lesser effect to those around him/her
(Many theories state that the Masked man has had considerable contact with T.O. and may have become 'Electro-statically charged' in a sense.)
~obsidalicious